In the late 1980s, he helped to form the New York-based punk band Bad Trip, releasing two full-length records and numerous EPs. When he began directing music videos, many bands and musicians noted that Siega's background in rock music was beneficial. He has worked with bands such as Weezer, System of a Down, P.O.D., Papa Roach, Blink-182 and The All-American Rejects. His 2000 video for Blink-182's "All the Small Things" earned him three MTV Video Music Award nominations and he was nominated for a Grammy Award for his Papa Roach video "Broken Home". In 2001, he signed with the award-winning commercial production company Hungryman Films and moved into the spot world.
Siega went on to direct films and acclaimed television series such as Dexter, True Blood, Cold Case and Veronica Mars. In 2008, he directed the pilot and co-executive produced The Vampire Diaries which ran for eights seasons on the CW Network. Siega also directed the pilots and was executive producer of The Following, Charlie's Angels, Time after Time, The Passage and God Friended Me.
Pretty Persuasion, the 2005 film he directed, was nominated for a Grand Jury Prize at the Sundance Film Festival and won the German Independence Award at the Oldenburg International Film Festival.

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